Plain white TDrake General Store1144 Queen St. W., 416-531-5042 (plus two other locations)
Organic American Supima cotton (made of the longest-strand, finest there is) weaves into an incredibly cozy, soft, wearable T-shirt. And yet it’s durable, which is what makes Shared’s plain white Ts the ideal everyday topper, whether the bottoms are a pair of cutoffs or well-cut work trousers. Shared’s Ts have a cult following: Leafs defenceman Dion Phaneuf and his starlet girlfriend, Elisha Cuthbert, have been known to buy them by the bagful. Appropriate for conscientious consumption—the shirts are knitted and sewn in the GTA—the goods don’t skimp on style: there’s a full lineup of crewnecks, V-necks, scoop necks and pockets, more than enough to keep the flightiest fashion fiend from ever getting bored. From $44.
Bargain bespoke suitLe Firme95 East Beaver Creek Rd., Richmond Hill, 905-707-8727
The first thing you’ll be asked at Le Firme is if you’re Italian. That’s because everything else at this Richmond Hill suit shop is: the Zegna cloth stacked on the walls, the complimentary espresso, the bolognese-red Fiat 500 parked out front, and the founder, John “The Bespokeman” De Laurentiis. He cut his chops at Harry Rosen in the ’70s and ’80s, and he’s eager to share his vast knowledge of bespoke suiting. The meticulous process, all done in-house with a designer and a team of tailors, takes about eight weeks and starts at $3,500.
Custom ShirtMarlon Durrant Bespoke Shirts193 Church St., 416-363-4868
Marlon Durrant is the perfect gentleman. From his Church Street studio, with its supple leather sofas, extensive single malt selection and smooth jazz on the radio, he sells his gentlemanly lifestyle to those in the know, one button-up at a time. Durrant learned his craft from a pair of venerable Italian-Canadian tailors more than a decade ago. He started his own custom shirt business out of a suitcase and quietly grew it into the city’s premier shirt destination, outfitting businessmen, athletes and entertainers. A single shirt is $350. A box of 14 is $3,500, or about $250 per shirt (with a bottle of Glenmorangie included).
(Image: Maja Hajduk)

EspadrilleChasse Gardée1084 Queen St. W., 416-901-9613
Britney Spears loves Los Angeles shoe designer Jeffrey Campbell’s skinny-wedged, all-one-piece-of-black-leather Pixie, and Lady Gaga, well, she prefers the Gaga, inspired by her. But Campbell’s edgy shoes have also earned a devoted following among non-celebrities, who like the look and price. At Chasse Gardée, Campbell’s new taupe Tick Espadrille merges his now-trademark soaring platform heels with the season’s demand for wicker and straw. The casual staple is suddenly badass. $145.

Raw DenimOver the Rainbow101 Yorkville Ave., 416-967-7448
It’s easy to include Over the Rainbow on this list. Possibly too easy. But it’s also the right choice: the long-standing Yorkville staple is the best place in the city to buy jeans. That includes the still-trendy rough, unwashed raw denim, made the same way as your grandpa’s indestructible Levi’s. Amid Over the Rainbow’s wall-to-wall stacks of blue (and sometimes black or grey) pants are some of the most important names in raw denim right now, including Swedish brand Nudie, Japanese denim powerhouse Edwin and Canadian favourite Naked and Famous, each of which offers a variety of models in both straight and skinny cuts. From $90.
(Image: Christopher Stevenson)

Summer loaferUncle Otis26 Bellair St., 416-920-2281
Uncle Otis and Swims loafers go together like Otis Redding and vinyl. For both the Yorkville store (named after the King of Soul) and the Norwegian footwear designer, the name of the game is upscale casual cool, apparel in the style of soul music. Swims is known for galoshes and recently started making loafers out of mesh and rubber. They’re water-resistant and relaxed enough for sitting on the dock of the bay, but stylish enough for getting the hell up and going someplace fancy too. $160.

Sun hatCabaret672 Queen St. W., 416-504-7126
The millinery equivalent of this summer’s maxi dresses is the enormous, floppy brim hat. What it lacks in subtlety it makes up for with superior sun protection. Vintage store Cabaret carries some of the most beautiful specimens in Toronto. During our recent visit, owner Tao Drayton had on display a shallow-crowned shear-straw version with red-tinted woven florets reminiscent of hats of the late 19th century. Although it isn’t technically vintage (Drayton guesses it was made in the past 20 years), it’s fancier than your average straw hat without being Royal Wedding showy. $175.
(Image: Carlo Mendoza)

SunglassesSpectacle752 Queen St. W., 416-603-0123 (plus two other locations)
Some of us love vintage sunglasses for the quality—mineral-glazed, scratch-resistant lenses and sturdier, heavier plastic frames—but the real appeal lies in shades you won’t see on anyone else. The most coveted at the moment are by Austrian designer Cari Zalloni, whose Cazal designs garnered an ’80s cult following. (“Snatchin’ Cazals” was a hit hip-hop single in 1985.) At press time, Spectacle had exactly one pair of vintage Cazal 867s. In perfect condition, they’re the ideal complement to asymmetrical haircuts and hemlines. $1,050.